Hugh Hefner’s Wives and Girlfriends Through the Years (Photos)

Hugh Hefner passed away Wednesday at 91-years-old and he sure did live a life fit for the founder of Playboy Enterprises.
Here are some of the wives and girlfriends of Hefner's past.

Twitter

Mildred Williams (1949-1959)
Hefner met Mildred Williams in college and they got married in 1949. The pair had two kids together. Williams had revealed that she had an affair while Hefner was serving in the army. He's said: “That was the most devastating moment in my life."
According to Hefner, his wife would let him sleep with other women to make up for her infidelity.
The two divorced in 1959.

Getty Images

Various women -- and men
Being, well, a playboy, Hef's love life can't simply be summed up with a list of "relationships" because he had numerous trysts that weren't so structured, with both women and men, including "maybe eleven out of twelve months' worth of Playmates" for a number of years after his divorce from Mildred. Marilyn Cole, Karen Christy and Lillian Mueller being some of the notable Playmates whose relationships with Hefner fall into that category.

Barbi Benton (1969-1976)
She landed a role on "Playboy After Dark" where she met Hugh Hefner. According to People, the two lived together for nine years and Hefner has said “I only regret not marrying Barbi,” said Hefner, “because it finally led to our going separate ways."

Carrie Leigh (1983-1988)
Leigh was Hefner's live-in girlfriend for five years before she left him and said that being in the mansion was "almost like a cult."

Getty Images

Kimberley Conrad (1989 - 2010)
Conrad married Hefner in 1989 and the pair had two children together. Nine years into their marriage, the two separated but remained legally husband and wife. After an 11 year separation, the two filed for divorce.

Getty Images

Mandy and Sandy Bentley (1999-2000)
The twin sisters were Hefner's first twin live-in girlfriends for a year. And yes we're saying "first" because they weren't the only ones.

Getty Images

Brande Roderick (2000-2001)
Roderick, a "Baywatch" actress before becoming Playmate of the Year 2001, dated Hefner for one year.

Getty Images

Holly Madison (2001-2008)
Holly Madison was Hefner's girlfriend for seven years. She moved in to the mansion when she was 21-years-old and left at the age of 28.
She was one of the original cast members of "Girls Next Door" along with Kendra Wilkinson and Bridget Marquardt.

Izabella St. James (2002-2004)
Izabella met Hefner when she was 26-years-old and in law school. She was invited to move into the mansion and become Hefner's girlfriend in 2002. She ended up writing a tell all book titled "Bunny Tales: Behind Closed Doors at the Playboy Mansion."

Getty Images

Bridget Marquardt (2002-2009)
Bridget was one of the original cast on "Girls Next Door" and dated Hefner along with Holly Madison and Kendra Wilkinson.

Getty Images

Kendra Wilkinson (2004-2008)
While dating Holly, Hefner was also dating Kendra and Bridget who were all cast members on "Girl's Next Door."
Kendra also detailed how she would often cheat on Hefner while they were together.

Getty Images

Kristina and Karissa Shannon 2008-2010)
The twins moved into the mansion in 2008 and were also part of "The Girls Next Door." Hefner apparently kicked them out of the mansion for having younger boyfriends come over.

Getty Images

Crystal Harris (2012 - 2017)
Crystal Harris and Hugh Hefner got married on New Year's Eve in 2012. He was 86-years-old and she was 26-years-old at the time. They were together until Hefner's death on Sept. 27.